1620568-13-9

Upstream product

• 76127-63-4 4-<<(Benzyloxy)carbonyl>methyl>-2-azetidinone 
• 178972-26-4 tert-butyl 4-isocyanatobenzylcarbamate 
• 1620568-12-8 C₂₅H₂₉N₃O₆ 
• 94838-55-8 tert-butyl (4-aminobenzyl)carbamate 

Downstream Products

• 1620568-15-1 C₂₀H₂₆N₄O₇ 
• 1620568-06-0 4-(2-(2-(carboxymethylamino)-2-oxoethyl)-4-oxoazetidine-1-carboxamido)phenylmethanaminium 2,2,2-trifluoroacetate 
• 1620568-14-0 C₂₇H₃₂N₄O₇ 

Relevant academic research and scientific papers

New β-Lactam Derivatives Modulate Cell Adhesion and Signaling Mediated by RGD-Binding and Leukocyte Integrins

A novel series of β-lactam derivatives that was designed and synthesized to target RGD-binding and leukocyte integrins is reported. The compound library was evaluated by investigating the effects on integrin-mediated cell adhesion and cell signaling in cell lines expressing αvβ3, αvβ5, αvβ6, α5β1, αIIbβ3, α4β1, and αLβ2 integrins. SAR analysis of the new series of azetidinones enabled the recognition of structural elements associated with integrin selectivity. We obtained selective and potent agonists that could induce cell adhesion and promote cell signaling mediated by αvβ3, αvβ5, α5β1, or α4β1 integrin, and antagonists for the integrins αvβ3 and α5β1, as well as α4β1 and αLβ2, preventing the effects elicited by the respective endogenous agonists.

Targeting integrins αvβ3 and α5β1 with new β-lactam derivatives

The αvβ3 and α5β 1 integrins are widely expressed in different cancer types and recognize the tripeptide Arg-Gly-Asp (RGD) motif present in several extracellular matrix proteins. We report here the design, synthesis and biological activity of some new β-lactam derivatives specifically designed to target integrins. The new molecules contain the azetidinone as the only cyclic framework armed with carboxylic acid and amine terminals spaced from 9 to 14 atoms to switch on recognition by integrins. All tested molecules showed a concentration-dependent enhancement in fibronectin-mediated adhesion of K562 and SK-MEL-24 cells; in particular 1, expressed a higher affinity towards α5β1 integrin (EC50 of 12 nM) and 2 was more selective for integrin αvβ3 (EC 50 of 11 nM).